If you wait 30 years to start budgeting for a roof, the house will rot into the ground from leaks before you have accumulated enough to replace it.

The time spent meeting pest inspectors, home inspectors, roof inspectors, HVAC guys, septic inspections, any contractors for work that needs done, photographers (paid by selling agent) signs and other marketing, Omissions and Errors insurance, MLS fees, NAR/CAR fees, car insurance, gas, only to have a deal fall apart over something.

However, for a rental property we may feel differently as it is an investment and not the roof over our head.

I’ve owned a dozen properties for almost 25 years and I’ve spent less than $500 on roofing, and zero on exterior siding/painting.

As for any oil tank, if they're leaking oil into the ground then yes you have an environmental issue to deal with. 

As is price point.. this will give you a better long term outcome.if you buy way under median your getting into renter dominated neighborhoods and schools for sure will be bottom ranked.. instead of going East have you considered Vegas.. lowest prop tax's basically in the country. no big weather issues  desert landscape super simple to take care of.. and Stucco homes with tile roofs no big thunder and wind storms to ruin roofs etc etc.. you can buy nice rental house there is a solid B location for about 300k. just worth checking out if you never have..

Did someone install too small a system, did the Freon leak out, are the air filters dirty. 

Hey Kris, Reach out through pm so you can send me all the details through email to see if I can help.Do you know the age of the mechanicals and the roof? 

Simply because there are more units and something like a basic roof replacement can be significantly more expensive as compared to a duplex.

If you find that you need to replace cabinet boxes, home depot sells unfinished birch that paints much nicer than the oak cabinets available at menards or lowes (oak can have tannins leak through and yellow the paint if not properly prepped if you use regular paint).